Triethylamine → 1-[(5-Chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine

HRID 352805Notes

Reaction equation

HRID 352805 reaction equation
Cl.[CH3:2][CH:3]([CH3:11])[CH2:4][CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][NH:6]1.[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:17]([S:31](Cl)(=[O:33])=[O:32])=[CH:16]2.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:23])=[O:24])[C:17]([S:31]([N:9]1[CH2:8][CH2:7][NH:6][CH:5]([CH2:4][CH:3]([CH3:11])[CH3:2])[CH2:10]1)(=[O:33])=[O:32])=[CH:16]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 227109842-(2-Methylpropyl)piperazine HydrochlorideHCID 235137375-Chloro-1-phenylsulfonylindole-2-sulfonyl chloride

Product 1

HCID 227110221-[(5-Chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a methylene chloride solution (150 ml) of 2-(2-methylpropyl)piperazine hydrochloride (1.50 g) were added 5-chloro-1-phenylsulfonylindole-2-sulfonyl chloride (2.72 g) and triethylamine (2.91 ml). The resulting mixture was stirred at room temperature for 13 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:20), whereby the title compound (2.69 g) was obtained as a brown oil.

Workup

  1. extractionthe water layer was extracted three times
  2. washwashed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customwas obtained as a brown oil

Sources & evidence

ORD record
ord-7b2a796e00cc4cc289c6465b350893d4
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…